


Let the Good Times Roll

by Alaskan_Assasin



Category: Supernatural
Genre: F/M, POV, Reader-Insert, Road Trip, Smut, Supernatural - Freeform, Vampires, i'm bad a tagging, refrence Dean/Reader/OFC, safe sex, talking about God with Cas
Language: English
Status: Completed
Published: 2016-04-25
Updated: 2016-04-25
Packaged: 2018-06-04 13:02:11
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,994
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6659080
Author URL: https://archiveofourown.org/users/Alaskan_Assasin/pseuds/Alaskan_Assasin
Summary: <blockquote class="userstuff">
              <p>The reader gets sent by Dean to work a haunting with Benny, when he can't join her. She gets the surprise of her life when it turns out Benny thinks that same about her as she thinks about him.</p>
            </blockquote>





	Let the Good Times Roll

**Author's Note:**

  * For [LizLovesLit](https://archiveofourown.org/users/LizLovesLit/gifts).



> A/N: I've been working on this sporadically for months, and finally think it's good enough to actually post. Let me know what you think.
> 
> I also want to thank the amazing LizLovesLit for her Beta services, and also for a far to long and drawn out discussion about if you could be turned into a vampire if you had sex with one.

When Dean suggested that I take Benny to check out a haunting in Georgia, while he and Sam hunted a Reaper in Wisconsin, I had some concerns. It was a haunting in some old Antebellum home in Savannah, meaning it was something I was prepared to take on alone. Benny and I had never worked a case together, since I usually went alone or with the guys, and had only spent time with Benny sporadically while in the company of others.

He seemed nice, polite, and I knew if he could get Dean out of Purgatory then he was certainly an asset in fight. It also hadn’t gone unnoticed by me that he was exactly my type, with his big shoulders and Southern charm. I tended to get out of the way when he was around. I was full of awkwardness and blushed when he looked at me, like a teenager with her first crush. The entire scenario made me uncomfortable, and I excelled at being uncomfortable. Not to mention that I hadn't exactly broached the subject of hooking up with one of the Winchester’s friends. Since Dean and I had a unique relationship dynamic, I wasn't exactly sure what the boundaries were.

“Come on Dean! I was hunting alone for years before you two bumbled into my life! I don’t need a babysitter, and I sure as shit don’t need someone I’ve seen naked suddenly start acting like my father. I already had one, I don’t need another.” I shouted at Dean as we walked towards the garage in the bunker, two pairs of boots thudding on the linoleum. He turned to look at me, putting a hand out to stop my progression down the hallway.

“Look, it’s not like I don’t trust you or think you’re incapable, ‘cause I know you’re great, honest. It’s just now you’re like a permanent part of the team, and if me and Sam aren’t with you I’d feel a lot better if you had someone we know watching your six. We tend to draw some fucking huge targets on our backs.”

“What about Cas?”

“Look, he’s great at dealing with the Big Bads, but more trouble than he’s worth on routine things. Just go with Benny, he’s already sort of close by, and he’s good in a fight.”

“Louisiana and Georgia are not ‘close’ Dean! Jesus! Why are you being so fucking pushy about this?”

“Why are you fighting this so much? You got beef with Benny?”

“No, I hardly even know him.” I shrugged, turning my face to look anywhere but at him.

“Wait a minute, you have the hots for him? I’m right aren’t I?”

“Firstly, no one says ‘have the hots’ anymore, you fossil. Secondly, what business is it of yours if I find someone attractive? Are you jealous of someone old enough to be my great grandfather?”

“If you’ll remember, sometimes it’s very important to me that you find someone attractive.” he smirked over at me. “Especially that hostess we met a few weeks back. And as for Benny's age, it’s not like that hasn’t stopped you before”

“Always thinking with your cock, Winchester. She was good though, I kind of wish we would have remembered to get her number. But, we aren’t talking about threesomes right now.”

“Aww, I always want to talk about threesomes.” he sighed wistfully.

“But Benny? That’s just crazy talk Dean!” I almost yelled. “Besides, I'm usually only into people who are into me too. I don't see any reason to go down a road that will just have a big ‘Dead End’ sign at the end of it.” He stopped his progression into the garage and turned to look at me, his expression surprisingly serious. He gently caressed my cheek, his eyes challenging me to keep contact with his.

“First off, everybody's ‘into’ you, you're fucking amazing, and if I didn't feel like you were just an incredibly irritating sister, whom I also happen to like seeing naked, I would be all over you, begging you to let me take you to dinner. Second, I already told him to keep his old vampire hands off of you.”

“Well, now I'm going to have to fuck him, just to piss you off.” I replied with a grin. “If I have to take Benny, then I’m insisting on a devil’s threeway next time.”

“It’s a deal Sweetheart.” he says, winking at me, and moving further past me into the garage.

“You know, I have always wondered what two Winchesters would be like.” I finished loudly, trying to keep the smirk on my face out of my tone. Dean twirled back towards with a look of pure indignation on his face.

“Now, that's never going to happen! Wait, what are you laughing about?”

“Hahaha, I may have run across a few stories on Tumblr written by someone named ‘mrsbeckywinchester’ when I finally found out about the whole meta book thing.” I giggled, wiping the tears from my eyes and trying to regain my composure. “And get that look off of your face, you look constipated.”

“Just quit being nasty with that shit.” He mumbles then turns around stopping next to a black muscle car. “Now, I just finished the engine rebuild on this one, so she’s all yours. Sam is jealous, but he can't shove his giant body in here.” He grabbed my duffle bag and walked towards the back of the Mustang, fishing the keys out of his pocket. He popped the trunk and motioned me closer.

“Ok, I already outfitted you with the basics back here in the false bottom. I even managed to grab you some holy oil, just in case.” he said, holding the clay amphora.

“Seriously?” I walked over to a bench in the corner and grabbed a red, plastic gas can. “Why you guys insist on keeping the oil in those things is beyond me.” I said as I pulled the cork and transferred the oil to the new container before closing everything back up.

“Huh,” he shrugged, “I guess I never thought of that.”

“Well, if Little Dean would quit thinking for Big Dean, then maybe these bright ideas would come to you.” I grinned as I shut the trunk, and moved towards the driver’s door. 

“Whatever, smart ass. Don’t you worry about Little Dean right now, there'll be all the time in the world for that when you get back. Let me know when you get there.” he said, before adding, “And continuing my part as overprotective old man, I got Cas to ride down there with you.” With that, he turned and walked over to the button to raise the door to the tunnel leading up to the surface.

Before he could make his full escape, I shouted “Ok, if I can't have some Wincest, then how about some Destiel?”. He walked out of the room without a backwards glance, flipping me off the entire way.

I turned the engine over and it rumbled to life with a growl that would put the Impala to shame. I pulled out of the tunnel and onto the road, working my way towards Interstate 49 taking me south toward Oklahoma City. Cas popped into the passenger seat before I even made it to the on ramp.

 

\---

 

Cas rode with me for three days, from the bunker all the way to Carencro, where Benny was living. I didn't want to admit it aloud, but I was beginning to enjoy my little roadtrip in the 69’ Boss 429 Mustang Dean had restored. I could feel his care for me, knowing he'd worked on it as a project for downtime in the Men of Letter’s garage, when he could have been doing any number of other things instead.

Cas spent a vast majority of the time the first day, entertaining me by telling me stories about the dawn of creation, and which parts of the Bible were pure fiction. To say I was horrified by the complete truth of Lot and his daughters would be an understatement. The story written in the bible isn’t near as sick and twisted as what really happened.

“Wait, there were goats too?” I asked incredulously. “Did he just fuck everything?”

“Mostly, there were some very confused sheep as well. But then he thought he should have sex with plants and what not. He ended up with quite an infection.”

“What?! Why?!” I wondered

“He was a very disturbed man, he thought the world had ended and he was free to fornicate however he wished. Luckily he died before he realized civilization continued, otherwise I'm sure he and his daughters would have been terribly embarrassed.” Cas continued.

“Well obviously! Now I feel slightly bad for teasing Dean about incest earlier.” I replied, completely unable to keep the giggle out of my voice.

“I fail to see the humor in such a joke, but you have always been one of those humans I can never seem to understand, no matter how hard I try.” He mumbled, looking out the window at the endless wheat fields of mid America.

After sometime, the ride became quiet, and Cas asked if I would like him to take over the driving for a few hours. Never one to turn down a cat nap, I agreed. At the next rest stop we pulled over so I could stretch, use the facilities, and switch seats.

“Do you require nourishment at this time?” he asked as I took a moment to rest against the trunk of the car, stretching my arms above my head and cracking the vertebrae along my spine. 

“If you could hand me my backpack out of the back seat, I have a few protein drinks in there."

“That is not real food, I will get you something.” he disappeared, only to reappear a few seconds later holding a grease stained paper bag in his hand, which he thrust in my direction.

“I assume this will be sufficient, it’s what Dean orders when he goes to a place where food is served.”

 

“You could just call it a restaurant Cas.” I laughed at his serious expression.

“Forgive me.” he said, looking abashed.

“Loosen up Cas. We might as well have some fun on this road trip.”

We got back into the car, stopping several hours later at a motel just north of Oklahoma City. I fell asleep quickly, not bothering to take my shoes off. I woke once during the night and noticed Cas reading the Gideon Bible from the drawer in the beat up night stand. He looked peaceful in the armchair - all covered in a soft yellow light from the small desk lamp in the corner of our room. While I rested he had slipped my shoes off and covered me in the unused half of the coverlet I was camped out on. I grabbed my headphones out of the bag I had haphazardly dropped next to the bed. Rolling over and hiding my head under the blanket, I plugged the headphones into my phone, pressing play on an audiobook to lull me back to sleep.

I woke just as the sun was peeking over the horizon. Cas had sat the book aside, and was now standing - peering out the window, watching the sunrise.

“I see the beauty in all of my Father’s creations, but I must admit that Oklahoma isn’t one of the best.” Cas said as I groggily rubbed my eyes.

“It kind of has a reputation for that, and tornadoes.”

“It’s confusing.”

I let out a laugh at that statement and at the consternation on his face.

The next 27 hours became kind of a blur, with almost 2,000 miles rushing by outside the window. We drove without stopping for longer than it took to fill up the car, with Cas driving through the night so I could get a few hours of sleep in the passenger seat. 

“I don’t know why you all insist on driving in these cars. It is slow, and taxing.” 

“Yeah well, as human, we don’t have much choice because none of us like your method of travel.” I replied.

 

“Regardless, it is still tedious.” Cas turned his attention back towards the road.

 

\---

 

 

Since first meeting the Cajun vampire several years ago, I had harbored my secret crush on him. He was big, confident, and the creole that came out of his mouth made me want him more than I had ever wanted another man. He had only ever treated me with respect, like you would treat your best friend’s kid sister. Which was funny, because I was two weeks older than Dean. 

However, I had no intention of ever making any kind of move towards him, both because of the death stare Sam and Dean give any man who talked to me, and since relationships have no business in a Hunter’s life, I had never had one. Not to mention that he only just returned from Purgatory for the second time. Instead, I had a few friends with benefits around the country, occasionally picked up someone for the night, or just snuck into Dean’s room for a little comfort and company. 

When we finally arrived, just south of Carencro, we turned off the highway and began driving down a dark road in the swamp. After several miles, the large vampire appeared in the headlights in the middle of the dirt road, waiting to be picked up. Benny and Castiel spent a few moments catching up while I sat in the driver’s seat and programmed the address in Savannah, Georgia into the GPS on the dashboard that Dean didn’t know about, because he would just complain about “douching her up”. Benny said goodbye to Cas, who gave me a friendly wave before disappearing, and folded himself into the seat beside me. 

“Nice car.” he said as he finally got the door shut. 

“Thanks. Dean rebuilt it, but Sam can’t fit, so I get to drive it.” I replied as I pushed the gas and took off down the road. 

“I can see that, there ain’t much room in this one.” he said.

“Yeah, but you should see the guys I can pull in it. It's almost to where I can't tell if they want me, or the car.” I laughed breezily.

“Well darlin’ I’m fairly certain they're after both. A beautiful woman, driving a vintage muscle car will get any man drooling.” he answered. “I was sure surprised when Dean called to tell me you wanted to take me on a hunt.” 

“He said what? God, I am going to fucking kill him for that.” I snapped. 

“Aww, suga’ he’s just looking out for you. Pretty girl like you, driving an amazing car, he probably just thought you needed a bodyguard to keep all those boys off of you.” 

“Well, believe it or not, I don't get bothered by fuckboys, probably because they can tell I’ll eat them alive.” I replied casually. 

“Maybe it's time you move along from the boys and start with men” he mused as the conversation died off.

We drove in silence for a few hours after that, because although Benny could go out in the sun, he lost most of his energy and strength. I went along with his plan to drive at night and catch a few hours of sleep at a hotel during the day. Resting in the passenger seat, my eyes drifted closed as I listened to him hum along with the Blues playing on the radio in the backwoods of Louisiana. The music and his gentle humming, along with the steady rocking of the car and the woodsy, smoky smell of Benny permeating the small space put me into a deep sleep. 

With a gentle nudge to my arm, he woke me just as the sun peeked over the horizon. He had pulled into the parking lot of a small, family hotel, and already had a room key in his hand. Ever the gentleman. he had also already walked to the trunk and taken out both of our small traveling bags, carrying both easily in one hand.

Groggy, I stumbled out of the car, reaching in to take my small emergency kit from behind my seat. 

“What’s that for Sweetheart?” Benny asked as I stood straight and shut the door behind me. 

“It’s just a small bag with silver, salt, holy oil, whatever I could need without having to unpack the back of the car. You never know when you are going to need something and I don’t want it to be stuck in the trunk when I do.” I replied. 

He lead me towards a room at the end and opened the door. The room was oddly nice, not a dust bunny to be found, and didn’t smell like cheap motel. 

“One bed? That’s a little presumptuous don’t you think?” I asked, giving him a side eye.

“Ha, well yes, I had thought of that, but the guy said this was the best room, so I thought you might appreciate it. It’s a big bed, but I’ll take the floor if it makes you uncomfortable.” he said. 

“I really couldn’t care less, but we’d better make sure Saint Dean doesn’t find out, he’ll think you besmirched my honor.” I joked. 

“Oh darlin’, Dean already gave me a lecture about your honor, and you know what I told him?” Benny asked. 

“What?” 

“I told him that you were a grown woman and could whatever you wanted with your honor” he said. 

I started laughing, laughing so hard I started crying and it took me a few moments to regain my composure. “Sorry, I was just imagining his face when you said that.” 

“But, now that I think about it, is there something between the two of you? I could go ask for another room.” He asked, a sheepish expression crossing his face. 

“Oh no. There is nothing even remotely romantic going on between me and Dean. We work together, hang out, fool around every now and then, but we aren’t a ‘thing’. I’m not super at relationships, or love, or anything even remotely normal when it comes to human sexuality and interpersonal dynamics.” I said. 

“You sure? Because I don’t want him coming after me for just sharing a bed with you.” he replied. 

“Look, he and I are just friends with benefits, with no deeper emotions to it. He has sex with other people, and so do I.” I said, with a smirk on my face. 

“So, are we still talking about just sharing the bed?” He asked, looking me in the eye and moving a few steps closer. His face had become incredibly serious and I could feel his warm breath on mine as I pondered the question he just asked. I decided to play dumb. 

“Ummmm, what do you mean?” 

He moved even closer, so that our bodies were touching and I could feel his heat radiating into me. My heart began to beat faster and my pussy started to throb with the arousal he was bringing out of me. 

“You’re gonna' have to calm down.” he said, his pupils blown with what could only be lust. 

“What? Why?” I whispered into the space between us. 

“Because your heart is pumping so fast it's almost deafening, and that along with that sweet smell in your panties, makes it hard for me to not take you right here, against this door.” he whispered back, his face moving closer and closer to mine before placing a soft, sweet kiss to my lips. He pulled back and asked “So, what do you think? I’ve wanted inside of you since the first moment I saw you.” 

“Don’t fall in love with me, I’m just not that kind of girl.” I replied somewhat breathlessly. 

“Well Darlin’ that’s an opinion I can get behind. Vampires ain’t no good at love anyway.” he answered as he brought his hands to my hips and pulled my body flush with his. His mouth came down on mine with force and I allowed him entrance when he licked along the seam of my lips. The kiss wasn’t hurried, or rough, but long and languorous. We stood there for what seemed like hours before his hands slowly started moving up my body to cradle my head when he moved in to deepen the kiss as my hands fisted the front of his flannel button down, feeling his strong chest move in and out with each breath. When he began to move his right hand back down my body, popping the button on my jeans, I pulled back suddenly. 

“I’m sorry Sugar, I didn’t mean to move so fast.” he said quickly stepping back away from where I was. 

“No, it’s not that. I just haven’t taken a shower in two days, and I really don’t want to get all ‘dirty’ while being actually dirty. Can we put this on pause for five minutes?” I asked as I slipped past him and over to my bag to grab my toiletries. 

“I could join you, get us both nice a clean.” he said with a quirk of his eyebrow and a grin.

“Have you ever taken a shower with someone while actually trying to get clean? It’s more irritating than sexy, I’ll be just a minute.” I said over my shoulder while walking towards the bathroom and gently closing the door. I took this opportunity to send Dean a text to tell them that I had met up with Benny and we were at a hotel for the day. 

Dean’s reply? “Don’t do anything I wouldn’t do.” And a dick pic. I snorted a laugh and sent a short reply before turning the music on my phone on to keep me entertained while I washed. 

The bathroom was huge, with a Jacuzzi tub and a walk in shower with more nozzles than seemed necessary. I made a mental note to myself to use both to their full advantage before hitting the road again as I fetched my shampoo and body wash. Thank goodness I had gotten a wax when Dean suggested we take a woman back to the hotel room last week, so I didn’t have to waste time shaving. It did take a while to untangle my curly hair, especially after days of sleeping on it and putting it up in a messy bun. I stepped out of the shower and wrapped myself in a towel just as the door slid open, revealing Benny leaning against the door jam. “Damn Sugar, and just when I thought I was going to get a sneak peek.” 

I grinned at that comment and moved towards the door where he deftly blocked my way. He drug his calloused hands up my arms and across my shoulders before slipping two fingers beneath the towel, right above my breasts, then pulling the towel free and letting it drop to the floor. 

“Oh Sweetheart, you look even better than I imagined. I could just eat you up.” he said, the pupils of his eyes so large they looked black, as he took a step back to take in my naked form, backlit by the bathroom vanity. He took another step back and I followed him until his knees hit the bed. I put my hands on his chest to push him over onto the bed and onto his back. 

“Laissez les bon temps roulet.” I said with a smirk before moving over him. 

“Now that’s what I’m talking about mo shou.” 

I straddled his hips and moved my hands under his shirt and felt his hard stomach and chest flex under my fingers. He sat up briefly and helped me remove his flannel and undershirt before laying back down and allowing me to continue the exploration of his chest. His hands roamed from my hips, up my back while I began to kiss his mouth in desperation to have some part of him, any part of him inside of me.

Suddenly, he sat up, and with his hand on my lower back, pushed my hips to rock against his still covered erection, letting out a soft moan at the friction caused. He pushed my upper body back until I had to put my hands behind me for support, my breasts put on full display for him. Grinning up at me, he closed his mouth around one nipple before flicking it with his tongue. He brought his hand up to my other breast and squeezed before giving that nipple a sharp pinch with his fingers. 

We rocked against each other like that for a long time, grinding into each other while he toyed with my breasts and peppered my chest with sharp bites, followed by warm, wet kisses over the marks he’d left. My orgasm started to build slowly, too slowly, and I groaned in frustration. 

“What’s wrong Darlin’? Need more?” 

“Yes” I said, in a whisper that sounded strangled and desperate. I couldn’t recall a time I had sounded like that before. Benny leaned back and pulled me with him until my center was situated on top of his straining, cloth covered erection. In this new position I could kiss his mouth, the taste of him was like a drug, causing me to quickly jump to the side and frantically work his jean buttons before pushing them, and his boxer briefs down his thighs. He lifted his hip to help and then kicked the clothing across the room. I pulled a condom out of my bag on the nightstand and rolled it over his hard cock.

He roughly grabbed my hips and moved me back over his straining erection. I hovered there for a moment, causing him to quirk an eyebrow at me in question. “And here I thought you would be all about the foreplay.” I said, before slowly sinking myself down onto him.

“Oh Suga’, let’s take the edge off, I’m going to make you feel so good that no other man will ever compare.” 

“Promises, promises” I said, before it was cut of by a low moan from deep in my chest as he pushed the rest of the way into me, my ass hitting his hips. Keeping his hands where they were, low on my waist, he began to rock me back and forth on his cock, pushing up his hips to grind against my clit on the upstroke. My fingers dug into his chest, scrambling to gain purchase so I didn’t collapse against him. But the feeling of him stretching and filling me was almost too much to take, especially after the slow warm up, and I slumped forward and rested my forehead onto his. 

His breath hit my face and the new angle rubbed my clit against him even more. My orgasm was ripped out of me as I gasped and groaned into his neck while he slowed and allowed me to come apart around him. 

When the worst of the trembling stopped, he rolled me over and pushed off of me until he was standing by the side of the bed. “Come here Sweetheart, bend over and let me fuck your sweet pussy from behind.” he said as I sat up and crawled over to him before turning around and presenting my ass, giving him a grin over my shoulder. 

Grasping his cock in one hand he guided it toward my wet entrance. He thrust in tothe hilt, in one swift motion and began pounding into me, chasing his own completion. “Fuck Benny! Harder!” 

He reached around and brushed his thumb across my clit a few times, before I was spiraling towards relief. “Benny, I… I’m gonna….. fuck!” 

“Come on Darlin’. I’m not going to stop until I feel you milk every drop out of my cock with your sweet pussy.” 

At that, I came again, harder than the previous two times, screaming his name into the mattress as his thrusts became stuttered and erratic and he came inside of me with a groan, before slumping down and resting his head on the center of my back. After a few moments he stood and rubbed my back and sides before pulling out. I lay there boneless, face down on the bed, while he moved around in the room behind me. A few minutes later I feel the bed dip under his weight as his hands moved over my back in a soothing way. 

“I brought you some things to put on if you want.” he said as he laid a pair of panties and a t-shirt next to my head. 

“Who knew you were so sweet?” I replied as I rolled over onto my back, grabbing the clothes before jumping up to go to the bathroom to clean up. When I returned to the room, Benny had decided on the side of the bed closest to the door. I scooted into the other side and quickly fell asleep while he watched baseball highlights on the television. I woke about 4:00pm, glad I had time to sit in that giant bath before we headed out, continuing our road trip to Georgia.

By the time I was ready to head out, I found Benny had already packed the car. I felt a warm smile flutter across my face while watching him talking to several teenage boys with the hood up when I finally left the room. As I walked out to greet them, the boys moved along down the parking lot. 

“Those kids sure liked this car, beautiful.” Benny turned to me with a grin. 

“Are you ready to get moving?” I asked, putting the rest of my stuff in the trunk. 

“Oh darlin’, I'm more than ready. I have a feeling this is going to be quite the trip.” He winked at me before climbing into the car and driving us off into the night.


End file.
